Alice and Andy in Block Island, RI

Planning a wedding on a slow-paced island that shuts down in the winter proved a challenge for Manhattanite Alice Birnbaum. But she and her fiancé, Andy Roebuck, couldn't think of a more beloved (or equidistant) place than Block Island to bring their New York and Massachusetts families together for a June celebration. The Spring House Hotel's sparkling shingles, promontory views of whitecaps, and ample space to accommodate many of the couple's nearest and dearest—183 people in all—made it a venue worth the year-and-a-half wait.

Guests sip cocktails and drink in the view from the 1852 Spring House, which has hosted notables such as Mark Twain and Billy Joel. Later, they migrated indoors for dinner and dancing to big-band tunes.